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6-MeO-THH

Chemical compound From Wikipedia, the free encyclopedia

6-MeO-THH, also known as 6-methoxy-1,2,3,4-tetrahydroharman, is a β-carboline (or more specifically a pinoline) derivative and a structural isomer of tetrahydroharmine (7-MeO-THH).[2] It is mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved), stating that 6-MeO-THH is very similar to the other carbolines.[1] The compound has been isolated from certain plants of the Virola family.[citation needed]

Other names6-Methoxy-1,2,3,4-tetrahydroharman; 6-Methoxytetrahydroharman
Routes of
administrationOral[1]
Drug classHallucinogen; Oneirogen; Serotonin receptor modulator
ATC code
  • None
Quick facts Clinical data, Other names ...
6-MeO-THH
Clinical data
Other names6-Methoxy-1,2,3,4-tetrahydroharman; 6-Methoxytetrahydroharman
Routes of
administration		Oral[1]
Drug classHallucinogen; Oneirogen; Serotonin receptor modulator
ATC code
  • None
Pharmacokinetic data
Onset of actionUnknown[1]
Duration of actionUnknown[1]
Identifiers
  • 6-Methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H16N2O
Molar mass216.284 g·mol−1
3D model (JSmol)
Melting point152–155 °C (306–311 °F)
  • CC1NCCC2=C1NC(C=C3)=C2C=C3OC
  • InChI=1S/C13H16N2O/c1-8-13-10(5-6-14-8)11-7-9(16-2)3-4-12(11)15-13/h3-4,7-8,14-15H,5-6H2,1-2H3 checkY
  • Key:RDUORFDQRFHYBF-UHFFFAOYSA-N checkY
 X markNcheckY (what is this?)  (verify)
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Use and effects

6-MeO-THH is reported to be hallucinogenic similarly to other β-carbolines like harmaline.[2] Limited testing suggests that it possesses mild psychoactive effects at a dose of 1.5 mg/kg (~100 mg for a 70-kg person) orally and is said to be about one-third as potent as 6-methoxyharmalan and three times as potent as harmaline.[2][3] Its dose range and duration are unknown.[1]

Pharmacology

Pharmacodynamics

Very little is known about the psychoactivity of 6-MeO-THH in humans. Studies in rats have shown it to bind to a number of serotonin 5-HT1 receptors and 5-HT2 receptors, dopamine D2 receptors, benzodiazepine receptors, and imidazoline receptors.[3][4][5]

Chemistry

Synthesis

The chemical synthesis of 6-MeO-THH has been described.[1]

Society and culture

Canada

6-MeO-THH is not a controlled substance in Canada as of 2025.[6]

See also

References

External links

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